Selected amidoxy compounds as flower preservatives

ABSTRACT

Selected compounds having an aminooxy group are useful in preserving cut flowers.

United States Patent 11 1 Beyer, Jr. et a1.

Dec. 30, 1975 SELECTED AMIDOXY COMPOUNDS AS FLOWER PRESERVATIVES Inventors: Elmo M. Beyer, Jr.; Bruno Quebedeaux, J r., both of Wilmington, Del.

E. 1. Du Pont de Nemours & Co., Wilmington, Del.

Filed: Jan. 19, 1973 Appl. No.: 325,091

Assignee:

References Cited UNITED STATES PATENTS Weissflog 71/68 Meyer 71/68 Ryan 1 71/68 Ellis 71/106 Fanzi et al. 71/68 Primary Examiner-Glennon H. Hollrah Attorney, Agent, or Firm-Anthony P. Mentis ABSTRACT Selected compounds having an aminooxy group are useful in preserving cut flowers.

4 Claims, No Drawings 2 SELECTED AMIDOXY COMPOUNDS AS FLOWER wherein R is H, hydrocarbyl or chlorohydrocarbyl of PRESERYATIV-ES a I y .up to 12 carbons; R is H or alkyl of up to l2'carbons; q and R? isrH, alkyl of up to 12 carbons, and ammonium, BACKGROUND INVENTION alkali metal and alkaline earth metal salts. These comp I 5 pounds are described in U.S. Pat. No. 3,282,987. 1. Field of the'lnvention. v, r H 3 Particularly useful and preferred for flower preserva- This invention relates to the extension of shelf life of tion are those of the above general formula wherein the flowers by the use of small amounts of aminooxy-con- R groups are hydrogen or 1-3 carbon alkyl groups. taining compounds preferably in the presence of a b. The oxadiazinediones, or their corresponding tausugar or an energy source. tomers, have; the formulas 3. O NR3 .R3CH N C C30 i C- R o N R 0 N J 2. Prior Arti wherein R is H or alkyl of up to 5 carbons and R is H,

Considerable effort has been made to extend the life alkyl of up to 5 carbons or amino-containing hydroof cut flowers. Flower preservatives that have "been carbyl of up to 5 carbons. These compounds are desuggested include energy sources (solublepolyhydroxy scribed in U.S. Pat. No. 3,238,200. It is noted these compounds such as sugars), ticidslbacte'ricids, fungilatter compoun s have been pr p r d from cides, metal ions, antioxidants, surfactants, plant horureidooxy compounds as described above by treatment mones such as the gibberellins, etcpAlthough some of with an alkali metal lower alkoxide. The a-ureidooxy these do extend the life of cutflowers, there is room for arboxy compound in turn can be obt ine from an additional improvement. a-aminooxy carboxylic compound of the formula DESCRIPTION OF THE INVENTION We have now found that compounds of the following I f R structures are effective in extending the life of cut flow- RJNHOCHCOOW ers:

wherein R is H, hydrocarbyl or chlorohydrocarbyl of H R X up to 12 carbons WlIICh are also useful as flower preserand vatives. These compounds are obtained by reaction of 3 o 3 o R c H N R R 3 c H N l I or its tuulomer l 3 O C C :0 C C -OR N R 0 N wherein the previously shown a-aminooxy carboxylic com- X alkyl or hydrocarbyl of up to 12 carbons or NHR pound (H NOCRHCOOR with hydrocarbyl acid with R being H, hydrocarbyl or chlorohydrocarbyl chlorides of 1-13 carbons including formyl, acetyl,

of up to 12 carbons; propionoyl, decanoyl, benzoyl, and p-chlorobenzoyl. R H or alkyl of up to 12 carbons; Preferably in the above compounds, the R, R, R, R R H, alkyl of up to l2 carbons, ammonium, alkali and R groups are H or alkyl of up to 4 carbon atoms.

metal or alkaline earth metalion; Extended flower preservation is facilitated by the R3 H or alkyl of up to 5 carbons; and v I addition of asugar (i.e., monoor di-saccharide), such R H, alkyl or amino-containing hydrocarbyl of up as sucrose, in amounts of 1-5% by weight based on the to 5 carbons; water solution.

These compounds are employed in aqueous solutions SPECIFIC EMBODIMENTS OF THE KNVENTION at a concentration of at least 1 ppm and generally less I than I000 ppm based on the weight of the solution. For f p l i amounts and maximum flower preservation, the solution is at a pH of q are speclfiedl are non'hmltatwe examples 0 4-5 and contains a monoor di-saccharide such as the mventlonsucrose, glucose, mannose, fructose, etc.

Included within the scope of this invention are ami- Example I nooxy compounds of the following types: Ohio White Sin carnations of 45 cm in length were a. The a-ureidooxycarboxylic acids and their derivaharvested at the tight bud stage. Five cm of the basal tives that are useful in flower preservation have the stem was removed and the fresh weight determined. formula Flower buds were dipped for 5 seconds in various solu- O I tions and two carnations were placed in 250 ml of each H g test solution in a graduated cylinder. Fresh weight and solution uptake were determined daily. With water as the control, a vase life of about 9 days resulted whereas with the methyl ester of Z-ureidooxypropionic acid at 100 and 500 ppm, a vase life of and 16 days resuited.

When the above procedure was repeated except that 1000 ppm of methyl 2-ureidooxypropionate was used, a vase life of about 17 days resulted. Addition of 3% sucrose to corresponding control and solutions containing 500 and 1000 ppm of the ureido compound gave vase life time of l 1 days (sucrose alone), 18 days (500 ppm of the ureido compound sucrose) and 19 days (for 1000 ppm of the ureido compound sucrose).

Example 2 Ohio White Sin carnations were harvested at the tight bud stage and the stems cut to provide a length of cm. The basal leaves were stripped and the flowers maintained overnight at F, then placed in sterilized 32 oz glass bottles each containing 250 ml of solution. The flowers were kept under constant incandescent light ft. candles) at room temperature of 7072F with humidity at 40-42%.

The-following table shows the vase life of the flowers with various adjuvants.

The embodiments of theinvention in which an exclusive property or privilege is claimed are defined as follows:

1. A method of extending the life' of a cut flower which comprises putting the cut stem end of a flower in an aqueous solution containing a compound of the formula i F H: NHO ncoocn Adjuvant (by weight) Vase Life (days) The compounds as defined in this invention are also useful for the preservation of other flowers, e.g., withroses the amount of adjuvant is generally much less than with carnations. Useful amounts are generally 1 to 100 ppm with roses.

3. The method of claim 1 in which the cut flower is a carnation.

4. The method of claim 1 in which the cut flower is a rose. 

1. A METHOD OF EXTENDING THE LIFE OF A CUT FLOWER WHICH COMPRISES PUTTING THE CUT STEM END OF A FLOWER IN AN AQUEOUS SOLUTION CONTAINING A COMPOUND OF THE FORMULA
 2. The process of claim 1 in which the compound is
 3. The method of claim 1 in which the cut flower is a carnation.
 4. The method of claim 1 in which the cut flower is a rose. 